Rosalino Balo, Andrés Fernández, David Reza, Pablo López, George W. J. Fleet, Ramón J. Estévez, Juan C. Estévez
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引用次数: 0
摘要
本研究报道了亚氨基糖 DAB 的合成以及 1-脱氢丹诺尻霉素(DMJ)和相应哌啶醇酸的歧化合成。关键步骤包括肼基羧酸苄酯和烯丙基胺分别对 D-木糖二呋喃酸酯和 D-葡萄糖二呋喃酸酯的双亲核置换。然后对生成的双环苷进行水解、氧化或还原。
Stable Ditriflates of D-Glucose in the Synthesis of Iminosugars and Polyhydroxylated Pipecolic Acids
A synthesis of the five membered iminosugar DAB and a divergent synthesis of the six membered iminosugar 1-dehydromannojirimycin (DMJ) and the corresponding sugar imino acid are reported. They involve double nucleophilic displacements of a D-xylose ditriflate by benzyl carbazate and a D-glucose ditriflate by allyl amine, respectively. They are followed by a similar protocol consisting of hydrolysis and oxidation or reduction of the resulting bicyclic glycosides. This allowed DMJ to be obtained from the cheap sugar D-glucose.
期刊介绍:
The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies.
The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry:
Liebigs Annalen
Bulletin des Sociétés Chimiques Belges
Bulletin de la Société Chimique de France
Gazzetta Chimica Italiana
Recueil des Travaux Chimiques des Pays-Bas
Anales de Química
Chimika Chronika
Revista Portuguesa de Química
ACH—Models in Chemistry
Polish Journal of Chemistry.